4-Hydroxy-3-methoxyamphetamine

HMA
Clinical data
Other names	HMA; 3-Methoxy-4-hydroxyamphetamine; MHA; 3-O-Methyl-α-methyldopamine
Drug class	Serotonin–norepinephrine–dopamine releasing agent
Identifiers
	IUPAC name 4-(2-aminopropyl)-2-methoxyphenol;
CAS Number	13026-44-3;
PubChem CID	197139;
ChemSpider	170725;
UNII	UW5V6G007J;
ChEBI	CHEBI:173516;
ChEMBL	ChEMBL1347;
Chemical and physical data
Formula	C10H15NO2
Molar mass	181.235 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(CC1=CC(=C(C=C1)O)OC)N;
	InChI InChI=1S/C10H15NO2/c1-7(11)5-8-3-4-9(12)10(6-8)13-2/h3-4,6-7,12H,5,11H2,1-2H3; Key:GPBOYXOSSQEJBH-UHFFFAOYSA-N;

4-Hydroxy-3-methoxyamphetamine (HMA), also known as 3-O-methyl-α-methyldopamine, is an active metabolite of 3,4-methylenedioxymethamphetamine (MDMA).^[1]^[2]^[3] It is substantially less potent than MDMA or 3,4-methylenedioxyamphetamine (MDA) as a monoamine releasing agent in vitro.^[4]^[5] Nonetheless, HMA has been found to induce the release of serotonin, norepinephrine, and dopamine with EC₅₀Tooltip half-maximal effective concentration values of 897 nM, 694 nM, and 1450–3423 nM, respectively, and hence acts as a lower-potency serotonin–norepinephrine–dopamine releasing agent (SNDRA).^[4]^[5] The predicted log P of HMA is 0.6.^[6]